How can sales drive customer success?

How can sales drive customer success?

Customer success is one of the most essential ingredients for sustainable growth in SaaS. Having a dedicated customer success manager (CSM) is great—but it's just as important that sales owns customer success too.

From a sales perspective, there are three main stages where customer success measures can be implemented:

  1. Pre-sell: before they're a customer
  2. Post-sell: while they're a customer
  3. Post-cancellation: after they're a customer

Before they're a customer

What can sales do before a deal is closed to improve customer success? How can sales drive customer success before a prospect converts into a paying customer?

Qualify for fit

As a salesperson, you want to close deals. It’s tempting to skimp on the qualifying part of the sales process. If a prospect shows interest, if you believe you can make the sale, clearly you should make the sale, right?

Not so fast my friend.

As a salesperson, it’s your job to sell to those who should buy your product, not to those who want to buy it!

Properly qualify prospects, and then ask yourself: Is this prospect really a good fit?

Example: Qualifying prospects

A prospect might come to us and say: “We need bulk email.”

The easy way to respond? “Oh yeah, great, we have this powerful bulk email feature! It’s going to make you a lot of money and save you a lot of time!” And then you push that prospect into becoming a customer.

But do you really understand what the prospect needs?

Instead, follow up with more qualifying questions.

  • What kind of bulk email do you want to send? Marketing, newsletter or sales bulk emails?
  • What kind of tracking, which metrics do you need on those emails?
  • Do you need HTML style emails or do you need text-only?
  • etc.

Asking these questions will help you determine whether that prospect is really a good fit or not.

If you sell to a prospect who isn’t really a good fit, just because they want “bulk email” and your product has “bulk email”, they’ll be in for a surprise if the bulk email function doesn’t match their use case.

And by that time they’ll have invested their time and money into your product—when you could easily have saved them both by asking some simple qualifying questions. The customer will cancel, and walk away from your company with a bad experience, and a bad taste in their mouth.

Qualify for risks

What are potential risks if this prospect becomes a customer? Can they really afford to stay with you? Can this customer survive long enough to truly be a valuable customer? What could potentially affect this customers’ lifecycle?

Example: Qualify for risks

At Close we had a new salesperson who sold a deal to a new startup. Our sales rep and that startup had something in common: they both lacked experience!

Startup: “We have no salespeople now, but we’re going to hire 30 interns, and have them cold call potential customers. So we’ll need 30 licenses for Close, and then by the end of the month, we’ll sort out the interns who didn’t make the cut, so we'll probably keep 15 to 20 licenses.” They had previously shared with us that they had received about $30,000 or $40,000 in funding.

Inside the mind of our sales rep: ‘Wow, 15 to 20 licenses, that could be $3,000 in MRR!’

He eagerly pushed to close the deal. “Look, here’s how we’ll do it. You put in your credit card now, and we’ll book you for 30 seats, but we won’t charge for you 30 days. After that, we’ll start billing your card for the remaining 15 to 20 seats.”

What happened next?

Before the trial even expired, 29 of the 30 licenses cancelled! One month we booked $3,000 in MRR, the next month we had to put in $2900 churn. Deals like that can totally screw up your numbers.

This salesperson should have qualified the risks! They should never have closed this deal. They could just have said: “Hey, do the trial, and after the trial—when you have your numbers down, and really know how you’re going to use Close—then we’re going to take your credit card number and close the deal, based on the actual number of users.”

Our salesperson should have realized that this was a high-churn risk customer:

  • With $30,000 or $40,000 in funding, they’d burn through their cash really quick, especially since they hired 30 interns!
  • Hiring 30 interns to do cold calling—without experienced sales leadership!—and expecting them to bring in deals isn’t going to work in the real world. They just didn't understand professional sales.

Two huge red flags. This is an extreme example, but it’s very common for salespeople to not properly qualify for risks, and it'll affect customer success later on.

Set the right expectations

Most sales reps sell benefits and make promises to prospects. But you want to take it a step further than that: set the right expectations for what being a customer of yours really entails.

Example: Ease of use

Prospect: “I want this product to do X, Y and Z easily.”

Sales rep: “Oh, great, this is super easy with our product, you are going to do great!”

When in reality, it might not be that easy, especially if your prospect isn’t tech-savvy, or doesn’t have the kind of expertise and experience you possess.

Understand where they are coming from:

  • Have they used a product in your category before?
  • Do they really understand the workflow they need?
  • Did you explain to them what the actual workflow is going to be?

Example: Promising benefits

Be mindful of how you convey your benefits.

Don’t say: “You’re going to see a 15% to 30% increase in productivity.”

Do say: “Our customers see a 15% to 30% increase in productivity on average.”

If you promise them 15% to 30%, and after using your product they get 10%, they’ll be disappointed. You will have disappointed them. In the worst case they’ll churn, but even if they stay, you’ll have screwed up the relationship. They’ll always take your word with a grain of salt, will always assume you’re overpromising, and they’re less likely to refer you. The impact you’ll have on them will be diminished because of lack of trust, and that can affect customer success later on.


Do you already have an onboarding process in place for your customers?

If not, create an onboarding experience ASAP, preferably a good training on how to use your product.

Example: Close onboarding

In the early days, we offered personalized 1-on-1 training sessions to all customers. As we grew and scaled, we started offering a weekly training webinar, where we cover different aspects of Close, and how to set it up and get going.

This training has been extremely popular, and it has been extremely effective at helping our customers become better at using the product, and getting more value out of it.

Why do you need onboarding?

It’s not enough to sell the benefits of your product. You also want to sell them the actual implementation.

Think about a diet product. You can say: “This diet system will help you to lose 30 pounds in six weeks!” They buy, and then you tell them: “Only eat carrots for six weeks, and go for a five mile run every morning.” Well, yeah, they would probably lose 30 pounds if they'd do that, but nobody is going to do it.

When customers start using your product, they are going to run into challenges. They are not going to fully understand how to use things optimally right from the start. It does require training. They need help configuring and setting things up optimally. If they aren’t using your product successfully, they will churn.

That’s why onboarding is so important.

Are you selling the onboarding experience?

If you DO have onboarding, then SELL the onboarding experience to your users! Don’t just passively offer the onboarding. Instead, proactively sell them on participating: push, convince and coerce them to do the onboarding!

At Close, every time we close a deal we tell them: “We’re very excited to have you on board! Now that you see the promise in the product, we want to also make sure that we deliver on this promise. The best way we can deliver is by helping you come on board and train you on Close, because it can be very complex and has a lot of nuances. So I highly recommend this Thursday, you do our training webinar, here’s the link, please sign up and have the entire team sign up, and whenever you add new users, please have them sign up.”

We’re selling our customers on the onboarding! It’s not enough to take their money now—we want to keep them happy, successful and productive, so that they stay onboard.

Sell your onboarding, so that your customers actually DO the onboarding!

Get long-term commitments

Get prospects to sign up for a long-term contract or annual plan. You want to get a long-term commitment from them so that all the work you invest into them pays off and they get a better price and more value.

But you have to sell this. Many startups fail at this—they assume customers are going to sign up for annual contracts by themselves if they want to, and make no serious effort to convert them to annual plans. “We’ll just give them an amazing experience with our amazing product and our amazing service, and they’re going to automatically stay!”

That’s not good enough.

Push people to sign annual contracts. Even before you close the deal. And if somebody came on board on a monthly plan, pitch them again in the next month on the annual plan, and say: “Hey, you’ve been with us for a month. How has the experience been?”

And if they’re happy with it, ask them: “Great, do you plan on using our product for the next 6 to 8 months?”


“Well, why don’t you save money and do a one-year contract with us, this way you’re going to be with us anyway, but you’re going to save ___ dollars.”

This is how you get more people to commit to annual plans, and reduce churn.

Later on when customers experience problems, they don’t just quit. They won’t be the fickle customer who just turns around and leaves when there’s an issue. And this is in their own interest as well, because switching from one vendor to the next is just going to slow them down, they'll have to change the way they work, and more often then not it's just an "out of the frying pan, into the fire" situation.

They’ll be more committed to finding a solution, and sticking with your product. It buys you more time to solve their problems and make them happy again, and it allows you to invest more effort into making them successful.

While they're a customer

Just because you’ve sold someone and they're now a paying customer doesn’t mean your job as salesperson is finished. Beautiful sales opportunities wait among your current customers—don't miss out! [Tweet this!]

Check in with customers you’ve closed a month or two ago. You want to find out:

  • How are they doing?
  • Is your product serving them well?


Ask your customers:

  • What's the plan for growth?
  • How many users are you going to add over the next few months?
  • What are other opportunities within this organization to sell this product? What about your support department? What about this other department?

Help your customers to put a plan together to bring more people on board.


Ask your customers if they can make referrals to other people in other companies who can also come on board.

Few salespeople do this, but if you consistently ask your current customers for referrals, it can become a substantial source of high-converting sales leads.

Let’s say a customer refers you, and you successfully sell to that referral. In addition to closing another deal, you’ll have accomplished several things:

  1. You have increased the perceived value of your product in the eyes of the referring customer. Since the person they referred obviously saw enough value in it to make a purchasing decision, others obviously too see the value in this. Don’t underestimate how much social validation matters, even in a professional B2B context.
  2. The referring customer (rightfully) feels they made an impact, they feel empowered because they made a difference. Thus, they’re more likely to make more referrals.
  3. Make the new (referred) customer thank the referring customer for making the referral and they're going to be even more excited to keep on referring you.

Problems and technical issues

You’re going to run into problems, especially if you’re working in a tech company. You’re going to have downtimes, things break, bugs … and your customers are going to get pissed off.

So how do you solve these problems? You either do it from a position of weakness, or from a position of strength.

From a position of weakness:

  • Apologize to your customers.
  • Fix the problem.
  • Try to compensate customers.
  • Apologize and beg for their mercy some more. :-(

From a position of strength:

  • Apologize to your customers.
  • Fix the problem.
  • Try to compensate customers.
  • Turn lemons into lemonade. :-)

Example: Close's calling outage

Our VOIP provider suffered from a DDOS attack. The calling function of our sales communication platform was down for an entire day. Now this is a very rare event, and our VOIP provider had never experienced this before. It affected all our customers with calling plans—they couldn’t make any calls from within Close.

Some customers complained vehemently. They were upset and angry about a day of wasted productivity and lost opportunities.

We did what any good software company would do: work furiously on resolving the issue, and communicate very transparently what was going on, what users should expect, and finally when the problem was fixed.

We personally gave extra attention to every single customer.

A crisis like this is your chance to shine.

Some of our customers demanded compensation for the productivity loss.

What most companies would say: “Of course, here’s a refund!”

What we said (and what every company who strongly cares about customer success should say): “All right, we’d love to help you guys out and actually strengthen this relationship. You can see how we responded to this situation and if you’re happy with the way we responded to it, here’s what we’re going to offer: we want to give you guys an additional 5 or 10% discount. But we want to make this a long-term relationship both ways, so that we can work on your success together. So we ask that you guys sign a one-year contract.”

We had five or six customers who demanded compensation.

How many do you think signed up for a one-year contract?


Always respond from a position of strength! Asking a customer for something in return is fair game. Contrary to what many people assume, it even benefits the customers, because it gives you more leverage to make them successful.

If you do it right, the relationship with these customers will improve, as was the case with the customers who took us up on "we’re sorry" offer. Just like in personal relationships, overcoming hard times together strengthens business relationships.

After they're a customer

All is not lost once a customer cancels. These make for some of the most challenging, but also most worthwhile sales conversations you can have. Skilled sales professionals have an opportunity to turn these customers around and make them successful with your product. Hustle hard to keep them on board, but don't go Comcast on them.

What do you do when a customer cancels their service with you?

First, you call them and ask them for feedback. You want to know what the issue is.

Second, you try to save the customer by communicating from a position of strength. Find opportunities to resolve the issue if you can. It’s worth it to invest effort into this.

At Close, every single customer that ever churns, we call and figure out exactly why they churn.

First thing is to understand: why did they churn? Understand what made them want to leave.

Example: Going out of business

Customer: “Well, we’re cancelling because we’re going out of business.”

Sales rep: “I’m sorry to hear that. Tell me a little bit more about this situation.”

And try to offer customers some help.

If it means that they just need to cut some costs for some amount of time, and then hopefully try to get their business back on track, then you might be able to help financially. Not by giving them money, but by giving them an extended trial or a discount. Sometimes a bit of generosity can give them the leeway to get back on track. But if they’re going out of business for good, give them advice, give them help, give them the support they need—you know how much sweat, blood and tears it takes to build something up, and how painful it can be to have it fall apart. Little gestures can go a long way.

Example: Missing feature X

Customer: “We’re leaving because your product doesn’t have feature X.”

Sales rep: “Ok, we didn’t have this feature. Did you know that our product lacks feature X when you first signed up? Did our sales do a bad job of understanding your needs? Did we do a bad job when it came to telling you whether or not we have all the features that fit your needs? Or is it something that you figured out later on, you just had a new need, and our product didn’t address this new need?”

The question here is: is that even part of your product roadmap?

Example: Close missing special reporting feature

Customer: “We’re leaving Close because we want reporting.”

Sales rep: “Ok, what type of reporting do you need?”

Customer: “We need reporting that graphs and charts how users are behaving based on X, Y and Z parameters.”

Sales rep: “Interesting. Now have you already found another tool that actually does that?”

Customer: “Yeah, we’re looking at this other tool that functions exactly this way.”

Sales rep: “All right, first let's step back and pause for a second. Why did you sign up with us to begin with? For what reason did you originally chose Close? What attracted you to us at first?”

Direct the conversation towards the benefits and the value of your product for the customer. This is simple sales psychology: it balances the equation a bit, and creates a counter-force to their desire to leave you. First understand why they chose you to begin with. Then understand what they specifically need, and where the mismatch is.

Sales rep: “All right, so you need this kind of reporting. How would that specifically work? What would that look like?”

Customer: “Well, X, Y and Z.”

Sales rep: “If we had exactly what you said, if we had it in this way, would you consider staying?”

Customer: “Yes, we would stay.”

Sales rep: “If we were able to deliver this feature in the next 2 to 3 months, would you consider sticking around for the next two to three months until you have that?”

SCENARIO A (feature is on roadmap customer negative):

Customer: “No, it’s just not worth it for us to keep on paying you for two or three months until you release feature X.” Sales rep: “All right, how about this, we’re going to give you a 30% discount for the next three months, until we release the feature. And if you’ve used the new feature for a month and it does everything you want and need, we’ll put you back on your current billing and you can be a happy customer again. And if feature X doesn’t do everything you want and need, or you’re just not happy with it for whatever reason, no problem, you can still move out to another software system of a vendor of your choice.”

SCENARIO B (feature is on roadmap, customer positive):

Customer: “Two or three months? Yes, we would consider staying!”Get them to stay (use incentives if necessary). Frequently update your customer on the progress you’re making towards releasing feature X.

SCENARIO C (feature is not on roadmap):

Customer: "Maybe."Sales rep: ”We’re not planning on launching this feature, but here’s a workaround you might want to try, if it works for you great, if not then on problem.”

You still want to ask the question though to make sure that the lack of feature is actually is the root cause! Remember, it's ok to not implement features some customers request.

What’s the strategy behind this?

It’s about aligning the customers’ expectations with the value you provide, and it creates a shared goal for you and your customer within a defined time frame.

These kinds of arrangements turn churning customers into valuable long-term partners, allies and brand ambassadors.

Example: Customer didn’t get enough support

Sometimes customers churn because they haven’t received the support and customer care they needed, or an issue they were struggling with didn’t get resolved well enough.

This is a great opportunity for you to sell them on you again.

Offer them extra value and attention.

Own up to your problem.

Sales rep: “Hey, we’re really sorry that his happened. We’re committed to making this work. Here’s what we propose. Give us two weeks. During this time, we’re going to give you an extra level of support, enterprise level of support—we’re going to give you support that we usually charge for. But you’re going to get it or free, we’re going to help you guys become successful, and deliver on the promise that we originally made you. Are you open to that, if we can do that, if we can fix that issue for you? If we can solve that problem for you, would you consider staying?”

Give them that level of support. Be rockstars. Overwhelm them with awesomeness. And then, at the end of those two weeks, make them sign a one-year contract.

Sales rep: “Hey, were you happy with the support we gave you?”

Customer: “Yes, we’re happy, your team was awesome. Our problems are solved.”

Sales rep: “Great! Why dont we make this a long term relationship? You saw how we solve problems, you saw how we deal with issues, why don’t we get you guys on board for the long run? We’re going to save you some money, and we’re committing to you to deliver amazing customer success.”

That’s how you not only save customers, but come out stronger at the end of that process.


You now know how to implement sales-driven customer success in all three customer stages: before they sign up, while they are paying you, and once they want to leave. Keep a healthy balance—don't discount your product, or overdeliver on service, to the point where it becomes unsustainable for you.

Are you struggling to keep up with the demands of your customer success program? Discover the latest customer success tools and technologies that can help you deliver better outcomes in this article.